Water → HCID 82418457, compound

HRID 712448Notes

Reaction equation

HRID 712448 reaction equation
[C:1]([CH:4]1[C:9](=O)[CH2:8][CH2:7][N:6](C(OC(C)(C)C)=O)[CH2:5]1)(=[O:3])[CH3:2].[NH2:18]O.Cl.O>CCO>[CH3:2][C:1]1[O:3][N:18]=[C:9]2[CH2:8][CH2:7][NH:6][CH2:5][C:4]=12

Participants

5

Reactant 3

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 53393266tert-Butyl 3-acetyl-4-oxopiperidine-1-carboxylate

Product 1

HCID 82418457HCID 82418457, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of tert-butyl 3-acetyl-4-oxopiperidine-1-carboxylate (1.50 g) and NH2OH.HCl (0.50 g) in anhydrous EtOH was heated to reflux for 0.5 h. The reaction mixture was cooled to rt, and then poured into 20 mL of water. The resulted mixture was extracted with CH2Cl2 (20 mL×3). The combined organic phases were dried over Na2SO4 and concentrated in vacuo, the residue was chromatographed with a silica gel column (eluting agent: 10:1 (v/v) DCM/MeOH) to give the title compound as yellow oil (0.45 g, 52.00%), HPLC: 90.00%. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 139.3 (M+1); 1H NMR (400 MHz, CDCl3) δ: 2.31 (s, 3H), 2.86 (t, J=8.0 Hz, 2H), 3.15 (t, J=8.0 Hz, 2H), 3.92 (s, 2H) ppm.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 0.5 h
  3. extractionThe resulted mixture was extracted with CH2Cl2 (20 mL×3)
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customthe residue was chromatographed with a silica gel column (eluting agent: 10:1 (v/v) DCM/MeOH)

Sources & evidence

ORD record
ord-86350758268448f19a0bda3340fe0a12
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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